Synthesis of 3‐CF3‐Indoles from HFO‐1234ze(E) via Cross‐Coupling and Intramolecular Cyclization

Author:

Mizuno Shota1,Yotsume Futa12,Kasahara Runa3,Inoue Munenori1,Ichikawa Junji1ORCID,Fujita Takeshi14ORCID

Affiliation:

1. Sagami Chemical Research Institute 2743-1 Hayakawa Ayase Kanagawa 252-1193 Japan

2. Department of Chemistry School of Science Kitasato University 1-15-1 Kitasato, Minami-ku Sagamihara Kanagawa 252-0373 Japan

3. Division of Chemistry Faculty of Pure and Applied Sciences University of Tsukuba 1-1-1 Tennodai Tsukuba Ibaraki 305-8571 Japan

4. Present address: The Institute for Solid State Physics The University of Tokyo 5-1-5 Kashiwanoha Kashiwa Chiba 277-8581 Japan

Abstract

AbstractThe synthesis of indoles with a trifluoromethyl group has attracted a lot of attention because they are promising structural subunits for pharmaceuticals and agrochemicals. As part of our project aimed toward the upcycling of hydrofluoroolefins (HFOs), we developed a method to construct a CF3‐bearing indole ring system through the Suzuki–Miyaura cross‐coupling of a brominated HFO‐1234ze(E) (CF3CH=CHF) with N‐tosylated o‐borylanilines, followed by nucleophilic 5‐endo‐trig cyclization at the vinylic position of the generated fluorostyrenes. We found that the Pd2(dba)3/SPhos catalyst system in the presence of K2CO3 and water in toluene afforded the corresponding 3‐CF3‐indoles in high yields in a one‐pot operation.

Publisher

Wiley

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